Dragon and the Devil's Due
by DelanaKiger
Summary: DeviantART Cuphead roleplay with SketchyDad. Grim Matchstick gets a visit from the Devil himself.
1. Chapter 1

**Hey, guys! DelanaKiger here! Guess what I just shamelessly partook in? A roleplay! :D Initially, I had thought roleplays were kinda, y'know... stupid (sorry if that offends anyone), but hey, don't knock something 'til you've tried it!**

 **Except for bugging people in their comment sections and stuff. Please don't do that if they don't want you to.**

 **On Sunday, I was on DeviantART looking at Cuphead fanart, and someone by the username of SketchyDad made a journal post titled "Cuphead Role Play Anyone?" I figured it would be both good practice and fun, so I went ahead and did a roleplay with him. :)**

 **I played Grim the dragon, and SketchyDad played the Devil, by the way. So, here's the whole thing!**

The day was nice and hot, perfect for a break. The Devil was walking out along a path near a tower, looking up at it with slight curiosity as he passed. To took a sip of a margirita. Thinking out loud. "Doesn't he owe me..."  
Glare.

Grim snored loudly in the top of his tower, unaware of the Devil down on the ground. He dreamed that he was fighting a knight over a pile of treasure. When Grim was about to win, his tower turned into the beach and the knight into a fish. The dragon grabbed the fish in his massive jaws and swallowed it whole rather anticlimactically.

The Devil grunted, making his way up the tower. It took him a great while but he made it up there. He poked Grim with his pitch fork.

Grim jolted awake with a small gasp, startled by the sudden force. He growled, hoping to look fierce to the intruder. But when he saw the Devil, Grim was the one who was scared. Gasping with fear, he immediately leaped back as far as the wall would let him.

"Wh-wh-what're you doing here, D-D-D-Devil!?" Grim stuttered, his voice a few octaves higher than normal.

The Devil leaned on the threshold. Looking up at Grim with eyes that pierced his skin but a smirk. "You know why I'm here Grim." He stood straight, walking twords him with a hum. "Don't tell me you, forgot."

Grim whimpered lightly like a dog as he glanced around rapidly and shivered. "N-n-n-no, I would never f-f-f-forget something so i-i-important," he replied, avoiding eye contact and rubbing his wrist. "I'm a, uhhhh... p-p-p-procrastinator."

The Devil popped a cigar in his mouth and lit it. Reaching up and grabbing his snout, pulling him down. "O, I hate procrastinaters~"

Terrified, Grim yanked himself free and rubbed his hurting muzzle. He began slowly side-stepping against the wall, hoping to make it to the door without the Devil noticing. "Y-y-y-you do?" He gulped.

He smirked devilishly. Stepping with him, reaching out a hand. "Your soul please~" his hand catching on fire

Grim hyperventilated, his mind racing. The Devil had clearly figured out Grim's plan of slowly advancing towards the door. He had to think of something quick. "What if I breathe fire on him?" he thought. "No, no, no, I would never win. What about smoke?" He blinked. "Yes, that should blind him long enough for me to get out," he thought.

Grim gasped loudly, getting as much air in his lungs as he could before blowing it all out as smoke, right in the Devil's face.

He fans the smoke from his face, mad now. He burst fire from the ground, his tongue lolling out as he laughed, pressing grim to the wall.

"I'M SORRY!" Grim shouted, tears beginning to pour down his face. "I sh-sh-shouldn't have done that! I-I-I-I'm just s-s-scared, that's all!" He crashed on the ground, covering his head as he trembled and wailed.

The Devil put a foot on his neck.  
"... you have a week, if your soul contract isn't in my grasp by next monday, I'll get it by force."  
He freed the dragon, blowing his cigar smoke in his face.

Grim coughed. "G-g-g-g-got it. S-s-s-see you M-M-M-Monday." The dragon didn't dare even look up for several seconds.

The Devil went to leave. "Oh... Grim... don't forget, if your not on time, you'll be punished."

Grim merely nodded timidly, his voice refusing to work.

The Devil left the room, walking back down the steps. "Ugh.. darn stairs..."

Grim's eyes darted, making sure the Devil was really gone. He hung his head, ears drooping. "Wh-wh-what am I g-g-g-gonna do?" he murmured.

There was a loud cream, the devil took a wrong step and it was a long fall.

 **I don't want this to be horribly long, so I'll just post multiple chapters.**


	2. Chapter 2

**Just so you know, I just copy-pasted from the roleplay, so not everything will be perfectly written.**

Grim gasped, startled by the noise. He debated inwardly whether or not to help the Devil, wanting to be on his good side but terrified to be anywhere near him. The dragon took a deep breath and rushed down the stairs, careful not fall down himself.

The devil stopped around the bottom, he was knocked out and his arm was broken, bleeding all over the steps. He was alive, thankfully.

Shivering, Grim peered out from behind a wall. He gasped when he saw how hurt the Devil was. Ears and head held down low, he crept towards the demon on all fours, fearful that at any moment he might wake up. Once he was standing next to the Devil, he slowly reached a hand forward to nudge him, immediately pulling back afterwards as though the furry humanoid was a wild animal that would snap any second. When he didn't, Grim leaned in closer, his ears lifting up somewhat.

Shaking and sweating, the dragon slowly lifted him up into his arms and silently carried him back up to the top of the tower. He set the demon down against a wall, wishing he had a bed or at least a chair.

Grim smiled a bit with hope. "Th-th-th-this should g-g-g-get me on his g-g-g-good side. Right?" he whispered.

The devil coughed, opening his eyes. He held his arm, where Grim thought he would lash out he just started crying. Hanging his head before sobbing awfully loudly, his horn snapped randomly, hanging by a thread. He trembled, in pain.

Grim backed up, still worried the demon would hurt him. The dragon's eyes darted with nervousness and confusion, his face growing more and more sympathetic. The Devil himself was hurting? To the point of crying?

Grim swallowed before his brain and voice finally worked together again. "A-a-are you o-o-o-ok?" he asked, unsure of what else to say or do.

The Devil looked up at him trying to wipe his tears but he tried moving his broken arm, it was agonizing. He howled in pain, biting his lip, pink tears flooding from his eyes. He tried to stand but he was too weak.

"G-g-gosh, that looks bad. M-m-m-mind if I take a look?"

The Devil didn't say anything for almost a full minute.  
"... p... please..."  
He tensed when they came up close to his arm, wheezing in pain

"I-I'm sorry!" the dragon apologized, immediately letting go. Grim flew to the other side of the room in a panic. "Y-y-you're not gonna hurt me for that, a-a-are you?" He panted, staring at the Devil with begging, frightened eyes.

The Devil whined.  
"I will if you don't help..." he said through gritted teeth.

Grim gulped. "P-p-point taken." With one last whimper, he walked up to the Devil and crouched to look at his wounds, wondering what to do before finally standing up.

"W-w-w-wait there." He turned to leave.

The Devil groaned, not wanting to be left alone but he was helping. He looked off, wiping his eyes just for more tears flooding.

About a minute passed before Grim came back with a first-aid kit and began bandaging the Devil's wounds.

"Th-th-there's only s-s-s-so much I can do," he explained as he worked. "I-I-I-I'll have to t-t-t-take you to the d-d-doctor after this."

The devil grunted once touched, but then he was done he grabbed Grim's arm, standing up and hugging him tightly with a good arm crying still.

Grim gasped and panted. He was about to retreat until he realized what the Devil was doing. He looked down at the demon, confused but relieved.

Grim lifted a finger. "Um..." He stopped; he had been about to ask if he still owed his soul or if this was payment enough, but not wanting to make the Devil angry for his ulterior motive, he decided against it.

"C-c-come on. L-l-l-let's get you t-t-to the doctor," the dragon said softly.

The Devil nodded, walking with him.  
He was quiet.  
"And no... you don't owe me your soul anymore..."

Grim stopped and blinked. "R-really? So I d-d-don't have to be scared of you anymore?"

"Not of me..." he waddled next to him, getting dizzy

Grim gently and silently nudged the Devil closer to him with his tail, waiting for him lean on the dragon's body for support before continuing to walk. The dragon's ears lifted up as he smiled with happy relief.

"Th-th-thank you."

The Devil smiled up at him, still crying.  
"Just- don't tell a single soul you saw me cry or I might change my mind"  
He leaned up on him, walking a bit better.

Grim chuckled nervously, unsure of whether the Devil was joking or not. "D-deal."

The Devil smiled. Looking up at him. "You can fly right...?" He said, still slightly pained.

Grim nodded. "D-d-do you want me to?"

The Devil nodded, getting on his back with some trubble. He had to say this, it's too perfict.  
"First time I ever got a ride before"  
Sad thing, it's true.

Grim chuckled nervously again. "W-w-well, tell me how you l-l-l-like it, I guess." He began walking down the stairs.

The Devil heald onto him with his legs and his good arm, when they made it to the bottom he had fallen asleep.

Grim stared at him in surprise when he heard the Devil's steady breathing. He began flying towards the doctor's office, hoping that flying wouldn't wake the demon up.

The devil was still out when they got there. The Desk worker watched him enter. "Hello how can I help yooo..." they saw them holding the devil and was put into panic, pressing a button to call out a doctor

The doctor came out and looked in confusion at the cowering desk worker. Then, he himself gasped as he saw the Devil. He took a slow step back, wide-eyed.

Grim raised his hands. "It's OK," he assured the doctor. "H-h-h-he's with me. He's b-b-b-badly hurt. Please, just treat him like you would any other p-p-p-patient."

The Doctor cautiously approached him. Taking him on a gurney and taking him back to operate.

After about an hour Grim was allowed to come to check on the devil, I'd he wanted too.

Grim nodded. "All right."

A nurse led him through the halls, the silence giving him time to think. He'd woken up a couple hours ago completely terrified of the Devil, only helping him to avoid being hurt himself, and now he genuinely cared if that horrible demon was okay.

"Maybe he's not so horrible?" Grim thought to himself.


	3. Chapter 3

The Devil was on his side, a huge cast on his arm. He seemed irritated by the bulky thing. He watched Grim walk in, trying to not be excited. "Oh, you stayed?"

Grim rubbed his arm shyly. "Heheh. Y-yes, I stayed. H-h-h-how are you feeling?"

"Could be better." He scratched under his cast slightly. "First time I shown up and they didn't screw me over. Last time they operated while I was fully awaje, the bastards..."

Grim's eyes widened. "R-r-r-really? Gosh, that's mean! I'm s-s-s-sorry you had to go through that. Will you have to stay in the hospital?"

"I'm not going too even if I need too." He sat up. "If I can stay awake through an organ transplant a broken arm won't bother me" he turned and got off the bed stopping in front of Grim. He took a deep breath, grabbing the dragons face and kissing it before exiting the room

"So, where are you g-g-g-gonna go? Back home?" Grim asked.

He stopped, looking at him. "I might go get a coffee. The Casino is my home and I'm taking a break." His tail flicked nervously

Grim gave a genuine smile. "W-w-w-want some company?"

He nodded gently. "That would be nice, yes..." he led him out the hospital, not signing out.

Grim felt somewhat bad breaking the rules of the hospital, but he didn't want to force the Devil to do something he didn't want to. He followed the demon with a glad smile, despite the fearful gasps and weird looks from others in Inkwell Isle.

The devil entered a small coffee shop. Walking up to the counter, waiting for someone to take his order... any minute now... a while passed and he started to get irritated. People had either run out in fear or were backed in a corner under a table. He wasn't about to leave till he was served

"Hey, it's okay, everyone," Grim said gently. "H-h-h-he's not here to hurt you."

"Did I react like this a few hours ago?" the dragon wondered.

The Devil leaned on the counter. Huffing in slight anger. A notepad was slid over for him to wright his order down, he glared, writing down this overly complicated thing. Turning to Grim. "You want anything?:

"Uh, j-j-j-just an e-e-espresso, please."

He nodded, writing down an even more complicated thing for that and sliding it back over to them. He leaned on the counter again, huffing in annoyance.

Grim's ears drooped with sympathy. He rubbed his wrist. "I'm real sorry p-p-p-people get so nervous around you. I'm a dragon, but I s-s-still can't say I know what that f-f-feels like."

"Its fine, you see the place i run?" The devil rubbed his horn- his horn- HIS HORN. it had to be snapped off at the hospital because it was unfixable. He started breathing heavily, getting real mad, the room getting hot.

Grim glanced around. "Uh, D-D-D-Devil? E-e-e-everything's getting real hot."

He gritted his teeth, smoke coming from his head, a small fire starting on it. He was making the room hot. They slid the coffee over and he handed Grim his coffee, and sipped some of his. There was no price, he growled. Guessing and leaving a 15. He stormed out.

Grim sighed and followed him out, unsure of what to say. So he just sipped his coffee, waiting for the Devil to say something first.

He just grumbled to himself, feeling at where his horn should be. He sat on a bench, when Grim went to sit next to him it burned like the sun. He looked up, seeing he hurt him, he tried to calm down. Patting his own face and sipping his coffee

Grim looked around, trying to think of a way to change the subject. He tapped his fingers hesitantly. "Umm... I-it's a... b-b-b-beautiful day t-t-today, huh?" he asked with a forced smile.

The Devil looked up. Grunting at the clouds. Leaning over the side, holding his broke arm. "I guess" he huffed. A lot calmer now, but still irritated.

"So... is there anything I can do to help?"

"No... no its OK Grim" he stood. Walking off.  
"Enjoy your coffee, I'm going to sleep."

And like that the devil sunk into hell for a rest.


End file.
